NDLI: Reductive Amination-Annulation Route to N-Substituted Dihydro-1,4-Benzoxazin-2-ones

Content Provider	Scilit
Author	Zidar, N. Kikelj, D.
Copyright Year	2008
Description	A synthesis of previously unknown 4-benzyl- and 4-alkyl-3,4-dihydro-1,4-benzoxazin-2-one derivatives 3 from the reaction of 2-(hydroxyphenylamino)acetates 1 with aldehydes 2 is described. The reaction proceeds by initial reductive amination of 1 with benzaldehyde derivative 2, followed by spontaneous lactonization to 3, which were isolated in moderate to good yields. The parent 3,4-dihydro-1,4-benzoxazin-2-one 4 was obtained by simple catalytic hydrogenation of 3 $(R^{¹}$ = H, $R^{²}$ = Ph). Compound 1 was obtained from corresponding aminophenol derivative and ethyl-2-bromoacetate.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2008-1077938.pdf
Ending Page	0797
Page Count	1
Starting Page	0797
ISSN	18611958
e-ISSN	1861194X
DOI	10.1055/s-2008-1077938
Journal	Synfacts
Issue Number	08
Volume Number	2008
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2008-07-23
Access Restriction	Open
Subject Keyword	Journal: Synfacts Organic Chemistry
Content Type	Text
Resource Type	Article

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Reductive Amination-Annulation Route to N-Substituted Dihydro-1,4-Benzoxazin-2-ones